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Top Rated Trails
near Jamaica Plain, Massachusetts
Jamaica Plain, Massachusetts 
Recommended Routes, Photos, & More
3.4
mi
5.5
km
#1Hemlock
Intermediate/Difficult
Allenstown Elementary School, NH
|
Intermediate/Difficult
|
Allenstown Elementary School, NH |
16
|
|
4.1
mi
6.6
km
#2Western Greenway (Metropolitan Pwky to Beaver St)
Intermediate
Belmont, MA
|
Intermediate
|
Belmont, MA |
25
|
|
0.5
mi
0.7
km
#3Wicked Hard Trail / Surf City
Very Difficult
South Peabody, MA
|
Very Difficult
|
South Peabody, MA |
4
|
|
1.5
mi
2.4
km
#4Orange Goose Loop
Difficult
Billerica, MA
|
Difficult
|
Billerica, MA |
7
|
|
|
0.7
mi
1.1
km
#5Orgasm
Difficult
Leominster, MA
|
Difficult
|
Leominster, MA |
3
|
|
|
2.7
mi
4.3
km
#6Moraine Trail - Northern Section
Intermediate
West Falmouth, MA
|
Intermediate
|
West Falmouth, MA |
3
|
|
|
1.0
mi
1.6
km
#7Gumpus Trail
Difficult
Dracut, MA
|
Difficult
|
Dracut, MA |
3
|
|
|
0.3
mi
0.4
km
#8Hellevator
Difficult
Tyngsboro, MA
|
Difficult
|
Tyngsboro, MA |
3
|
|
|
1.3
mi
2.1
km
#9Northwest Trail
Difficult
Sharon, MA
|
Difficult
|
Sharon, MA |
3
|
|
|
0.6
mi
0.9
km
#10Coal Road Singletrack
Difficult
Belmont, MA
|
Difficult
|
Belmont, MA |
10
|
|
|
1.1
mi
1.8
km
#11Morses Pond Trail
Intermediate
Wellesley, MA
|
Intermediate
|
Wellesley, MA |
2
|
|
|
0.6
mi
1.0
km
#12Rogue Dead Guy
Difficult
Cohasset, MA
|
Difficult
|
Cohasset, MA |
2
|
|
|
0.3
mi
0.5
km
#13Fridge Door
Difficult
Bedford, MA
|
Difficult
|
Bedford, MA |
2
|
|
|
0.8
mi
1.4
km
#14DNA Trail
Intermediate
West Warwick, RI
|
Intermediate
|
West Warwick, RI |
2
|
|
|
1.3
mi
2.0
km
#15Haunted Hollow
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
1.0
mi
1.6
km
#16Twister
Difficult
Granby, MA
|
Difficult
|
Granby, MA |
2
|
|
1.2
mi
1.9
km
#17Moose Alley
Easy/Intermediate
Pocasset, MA
|
Easy/Intermediate
|
Pocasset, MA |
2
|
|
|
0.2
mi
0.3
km
#18Upland Trail
Intermediate/Difficult
Marblehead, MA
|
Intermediate/Difficult
|
Marblehead, MA |
2
|
|
|
0.6
mi
1.0
km
#19Demon Pond Trail
Difficult
Northwood, NH
|
Difficult
|
Northwood, NH |
2
|
|
|
0.4
mi
0.7
km
#20Thrush
Intermediate
Tolland, CT
|
Intermediate
|
Tolland, CT |
2
|
|
|
0.4
mi
0.6
km
#21Root Trail
Difficult
Danielson, CT
|
Difficult
|
Danielson, CT |
2
|
|
|
0.7
mi
1.2
km
#22Big Bear in Bear Brook State Park
Intermediate
Allenstown Elementary School, NH
|
Intermediate
|
Allenstown Elementary School, NH |
7
|
|
|
0.6
mi
1.0
km
#23Poet's Seat Tower Access Road
Intermediate
Greenfield, MA
|
Intermediate
|
Greenfield, MA |
1
|
|
23.4
mi
37.7
km
#24Air Line State Park Trail
Easy
East Hampton, CT
|
Easy
|
East Hampton, CT |
1
|
|
|
0.4
mi
0.7
km
#25Awesome-Sauce Trail
Very Difficult
Saugus, MA
|
Very Difficult
|
Saugus, MA |
1
|
|
|
1.0
mi
1.6
km
#26Wolf Den Hill
Difficult
Princeton, MA
|
Difficult
|
Princeton, MA |
1
|
|
|
0.4
mi
0.7
km
#27Doggy Trail
Intermediate
North Falmouth, MA
|
Intermediate
|
North Falmouth, MA |
1
|
|
|
2.2
mi
3.6
km
#28Peabody Loop
Intermediate
Dover, MA
|
Intermediate
|
Dover, MA |
1
|
|
|
0.7
mi
1.2
km
#29Tyler Trail
Difficult
Berlin, MA
|
Difficult
|
Berlin, MA |
1
|
|
|
1.1
mi
1.8
km
#30Madbury Trail
Intermediate
Madbury, NH
|
Intermediate
|
Madbury, NH |
1
|
